N-Formylmorpholine → HCID 15322096, compound

HRID 1613615Notes

Reaction equation

C([Li])(C)(C)C.Br[C:7]1[CH:8]=[CH:9][C:10]2[O:16][CH2:15][CH2:14][CH2:13][CH:12]([OH:17])[C:11]=2[CH:18]=1.[CH:19](N1CCOCC1)=[O:20]>CCCCC.C1COCC1.C(OCC)C>[CH:19]([C:7]1[CH:8]=[CH:9][C:10]2[O:16][CH2:15][CH2:14][CH2:13][CH:12]([OH:17])[C:11]=2[CH:18]=1)=[O:20]

Participants

Conditions

Temperature: -78 °C

Procedure

254 ml (0.6 mole) of a 1.7 molar solution of tert.-butyllithium in n-pentane is slowly added dropwise under argon to a stirred solution of 48.6 g (0.2 mole) of 7-bromo-5-hydroxy-2,3,4,5-tetrahydro-1-benzoxepin in 550 ml of absolute THF at -90° C. to -100° C. The mixture is subsequently stirred at -78° C. for 1 hour and then, at this temperature, a solution of 24 ml (0.24 mole) of N-formylmorpholine in 180 ml of absolute THF is added dropwise while stirring vigorously. The mixture is stirred at -78° C. for 1 hour and subsequently allowed to warm to 0° C., and is diluted with diethyl ether and hydrolyzed with ice-water. After extraction several times with diethyl ether, the combined organic extracts are washed with water and saturated brine and dried over sodium sulfate, and the solvent is stripped off in vacuo. 40.7 g of yellowish oil are obtained and reacted further without purification.

Workup

stirringwhile stirring vigorously
stirringThe mixture is stirred at -78° C. for 1 hour
temperatureto warm to 0° C.
extractionAfter extraction several times with diethyl ether
washthe combined organic extracts are washed with water and saturated brine
dry with materialdried over sodium sulfate

Sources & evidence

ORD record: ord-d5a944520e0e42d0afacac9095d10382
Source dataset: uspto-grants-1993_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05194442

Reaction notes

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